Benzenamine, N,N-dimethyl-3-nitro-
- Formula: C8H10N2O2
- Molecular weight: 166.1772
- IUPAC Standard InChIKey: CJDICMLSLYHRPT-UHFFFAOYSA-N
- CAS Registry Number: 619-31-8
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Aniline, N,N-dimethyl-m-nitro-; m-Nitro-N,N-dimethylaniline; Benzene, 1-(dimethylamino)-3-nitro-; N,N-Dimethyl-m-nitroaniline; N,N-Dimethyl-3-nitroaniline; 1-(Dimethylamino)-3-nitrobenzene; 3-Nitro-N,N-dimethylaniline; NSC 9814
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 17.4 ± 0.43 | kcal/mol | Ccb | Furukawa, Murata, et al., 1984 |
Condensed phase thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -4.80 ± 0.43 | kcal/mol | Ccb | Furukawa, Murata, et al., 1984 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1089.2 ± 0.36 | kcal/mol | Ccb | Furukawa, Murata, et al., 1984 |
Phase change data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 555.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 333.65 | K | N/A | Beringer, Brierley, et al., 1953 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 22.2 ± 0.07 | kcal/mol | C | Murata, Sakiyama, et al., 1985 | AC |
ΔsubH° | 22.16 ± 0.065 | kcal/mol | C | Furukawa, Murata, et al., 1984 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.5 | 442. | A,GS,EB | Stephenson and Malanowski, 1987 | Based on data from 427. to 558. K. See also Andon, Biddiscombe, et al., 1960.; AC |
11.5 | 372. | N/A | von Terres, Gebert, et al., 1955 | Based on data from 357. to 492. K.; AC |
Gas phase ion energetics data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 213.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 207.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.984 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -22.0 kcal/mol; ΔSea =-2.0, est. from data in Chowdhury, Heinis, et al., 1986; B |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Furukawa, Murata, et al., 1984
Furukawa, J.; Murata, S.; Sakiyama, M.; Seki, S.,
Thermochemical studies on 3- and 4-nitroanilines and their N,N-dimethyl derivatives,
Bull. Chem. Soc. Jpn., 1984, 57, 3058-3061. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Beringer, Brierley, et al., 1953
Beringer, F.M.; Brierley, A.; Drexler, M.; Gindler, E.M.; Lumpkin, C.C.,
Diaryliodonium Salts II. The Phenylation of Organic and Inorganic Bases,
J. Am. Chem. Soc., 1953, 75, 2708. [all data]
Murata, Sakiyama, et al., 1985
Murata, S.; Sakiyama, M.; Seki, S.,
Sublimation calorimetric studies using a calvet microcalorimeter,
Thermochimica Acta, 1985, 88, 1, 121-126, https://doi.org/10.1016/0040-6031(85)85419-8
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Andon, Biddiscombe, et al., 1960
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F.,
1009. Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols,
J. Chem. Soc., 1960, 5246, https://doi.org/10.1039/jr9600005246
. [all data]
von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W.,
Brennst.-Chem., 1955, 36, 272. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr.,
Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN],
J. Am. Chem. Soc., 1985, 107, 2291. [all data]
Chowdhury, Heinis, et al., 1986
Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P.,
Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A- + B = A + B-,
J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
EA Electron affinity Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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